• Work
  • Writing
  • Info
Menu

Brandon Oxendine

  • Work
  • Writing
  • Info
×
Photo by Randy Fath

Photo by Randy Fath

The First Year Leading Design at a Startup

Brandon Oxendine July 25, 2019

It’s a struggle joining a new team, especially when you’re meant to lead it. I documented my ideal first year as a design team lead for my own reference and thought I’d share it for yours.

Just a note before we get started: there’s not a whole lot of predictability in the first year at a new job. This is meant more as a guideline than a recipe. These are things you should keep in mind along a rough timeline, along with potentially helpful ways to measure your success along the way. Your mileage will definitely vary.


Establishing vibes

1. Get to know the team.

Measure: Team cohesion (via survey)
  • Grab 15 minutes on each designer’s calendar to chat 1-on-1 as soon as possible

  • Discuss things they like to do outside of work

  • Ask them to walk you through projects they’ve worked on since they’ve been here

  • Understand their career history and define career goals

  • Understand where people feel they are being underutilized—find out where they would like to be utilized more

  • Understand each designer’s strengths and weaknesses. Share your own personal strengths and weaknesses to open an honest dialogue. The result should lead to everyone getting to know each other better and the team working more efficiently on things that make sense for their strengths.



2. Schedule weekly recurring 1-on-1 check-ins with each designer

Measure: Retention and promotion of designers in the organization
  • Keep a pulse on the whole team

  • Review work made in the last week

  • Offer professional, career, or design advice

  • Be available for questions, thoughts, concerns, or career growth questions



3. Schedule weekly design critiques

Measure: Effectiveness of critiques (via survey)
  • Designers often are either working with stakeholders or staying in their zones all day. They rarely get uninterrupted blocks to chat with other designers about things they’re working on. This weekly critique is a place to ensure that’s possible. If you’re a remote team, catch-ups like this are vital for team cohesion and vibes

  • Deep dive on features in progress and provide helpful feedback

  • Stay visually in sync



4. Define a shared sense of purpose that everyone can agree on and get behind

Measure: Percentage of people who believe we work by our purpose statement
  • North star to reference when things are unclear

  • This might include a master design prototype of what we want to work towards as a team

  • Do a survey of the team to get larger buy-in before defining something that affects everyone

  • Work directly with leadership to define this purpose statement

  • Make this clear and accessible to anyone within the company


Building trust

1. Ensure you personally have buy-in and are empowered to do your job effectively from leadership

Measure: Time from design brief to launch
  • Schedule monthly recurring 1-on-1’s with leadership

  • Keep leadership informed about the vision and direction of the design team

  • Set quarterly goals and get early buy-in before projects begin

  • Listen to the ideas and concerns of leadership



2. Design and implement an official design onboarding process

Measure: New hire onboarding satisfaction survey after 3, 6, and 12 months
  • Each member of the team should go through this

  • Everyone starts from the same foundation, doesn’t feel lost in their new role, and feels valued

  • This should be a long-term onboarding that covers day one to year one, not just setting up their computer



3. Build a list of design improvements and opportunities

Measure: Number of design bugs resolved
  • Do an extensive QA pass on all the offerings of the company

  • Set up a design bug backlog that anyone can grab from when there’s downtime

  • Align with engineering and design on priorities and organize work into upcoming sprints



4. Understand other teams’ problems, articulate solutions, and create value

Measure: Number of design briefs received vs. resolved
  • Put in place a system where other teams can submit design briefs

  • Make sure these briefs are accessible to everyone and standardized

  • Respond in a timely manner to those briefs, and show results after project is complete



5. Introduce monthly “Design Show & Tell”

Measure: Company-wide understanding of what the design team is working on
  • Designers and researchers can present to the whole organization and explain thinking and execution behind their projects

  • This opens up the process to the larger organization by showing people what we’re working on

  • Makes the larger organization feel like part of the design process


Make change

1. After trust and familiarity is built, implement new design processes

Measure: Time from brief to handover
  • Organize the team into product-focused teams, with designers focused on specific parts of the experience

  • Switch the team to centralized design software that makes it easy to build and maintain a cohesive design system. Figma is best for teams for many reasons.

  • Make design process clearly defined, public, and easily able to reference for everyone at the company



2. Define a path for individual contributors

Measure: Retention of individual contributors
  • Define a path for development for individual contributors that allows them to advance in level and pay grade without having to become a people manager

  • Develop product experts who are able to tackle deeper problems within the organization

  • Plan time for designers to work on their own ideas for fun



3. Promote authentic user empathy around the whole company

Measure: Internal net promoter score
  • Build a home for user research, where research is clearly displayed

  • Invite members of the larger organization to sit in on user research studies

  • Start initial user research with members of the company



4. Build a design system and make it public

Measure: Adoption among design and engineering teams
  • Ensure internal team is always on the same page

  • Increase design consistency within the product

  • Make the design system public, and position the company as a leader in the design community


If this helped you at all or you have more ideas on how this might be made better, reach out on Twitter.

← The Pessimist’s Design SprintProcess →

Just been bangin’ around in here from 2008—2025.

🤙